Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (9): 1753-1758.DOI: 10.6023/cjoc1201071 Previous Articles     Next Articles

Notes

新型龙胆酸衍生物的合成及其抑制酪氨酸酶活性研究

宋长伟a, 熊丽丹b, 王裕军a, 张南b, 李霞a, 李颖a, 李利c, 尹述凡a   

  1. a 四川大学化学学院 成都 610064;
    b 四川省化妆品工程技术研究中心 成都 610064;
    c 四川大学华西医院皮肤科 成都 610041
  • 收稿日期:2012-01-07 修回日期:2012-05-11 发布日期:2012-03-14
  • 通讯作者: 李利, 尹述凡 E-mail:chuandayouji217@163.com

Synthesis and Inhibition of Tyrosinase Acitivity of New Gentisic Acid Derivatives

Song Changweia, Xiong Lidanb, Wang Yujuna, Zhang Nanb, Li Xiaa, Li Yinga, Li Lic, Yin Shufana   

  1. a College of Chemistry, Sichuan University, Chengdu 610064;
    b Sichuan Province Cosmetics Engineering Technology Research Center, Chengdu 610064;
    c West China Hospital, Sichuan University, Dermatological Department, Chengdu 610041
  • Received:2012-01-07 Revised:2012-05-11 Published:2012-03-14

To discover new whitening active compounds, ten novel 2-hydroxy-5-alkyl(H)oxybenzoic ester derivatives (3a, 3b and 6a~6h) were prepared via the starting materials of methyl gentisate, alkyl halides and α-hydroxy acid ethyl ester. Their chemical structures were confirmed by 1H NMR, IR, MS and HRMS techniques. The preliminary bioassay test demonstrated that compounds 6a, 6b, 6e and 6f had stronger inhibition of tyrosinase activity. Further pharmacological experiments showed that after substitution modification of compounds 6a~6h, their toxicity and phototoxicity are lower than methyl gentisate and hydroquinone.

Key words: white, gentian methyl, tyrosinase, toxicity, optical toxicity